He did so for Jeb Bush in 1998, holding a high-dollar fundraiser for the gubernatorial candidate in Trump Tower and shelling out $50,000 to the Florida Republican Party. But when Bush took office in 1999, Trump didn't get the political help he needed to make his casino dreams a reality in the Sunshine State.
Instead, Bush maintained his hardline stance against gambling in the state, delivering a death blow to Trump's hopes of building out a multi-million dollar casino endeavor with the Seminole Tribe of Florida and prompting him to abandon those plans.
"It certainly had a chilling effect," Doug Guetzloe, a Florida political consultant who worked for the gaming giant Bally Entertainment in the '90s, said of Bush's election. "Gov. Bush made it clear to everyone that he was not interested in having casinos in the state of Florida ... the word definitely went through."
As Trump and Bush now lock horns in their fight to secure the Republican presidential nomination, the casino episode illustrates that the animus between the two men took root far before the 2016 race.
Florida's laws prevented casinos from expanding their offerings from bingo-style games to wider gambling operations, and when Bush was elected in 1998, he made clear none of that would happen on his watch.
"I am opposed to casino gambling in this state and I am opposed whether it is on Indian property or otherwise ... The people have spoken and I support their position," Bush told the St. Petersburg Times, now Tampa Bay Times, in 1999, referencing the three failed referendums to approve casino gambling.
Trump abandoned his hopes to expand the casino business in Florida not long after Bush's election. Mallory Horne, a former Florida statehouse speaker and Senate president whom Trump had hired to lobby on his behalf of his gambling interests in the state, told the magnate that those prospects were dead, according to legal filings
obtained in 2005 by Bloomberg Business in connection with a lawsuit Trump filed against a former associate.
But Bush's hard-nosed opposition to any relaxing of Florida's tight control on gambling came despite Trump's fundraising efforts on Bush's behalf.
Trump hosted a $500-a-head fundraiser boosting Bush's gubernatorial campaign in December 1997, according to several news reports from that time. That fundraiser and subsequent out-of-state donations helped Bush double his Democratic rival's fundraising haul in the subsequent campaign-filing period.
The next year, as Bush continued to campaign for governor, Trump donated $50,000 to the Florida Republican Party. And through it all, Trump employed Horne to lobby on behalf of his gambling interests in the state.
It's not clear that Trump's political contributions were aimed at needling Bush and Republican lawmakers toward a more flexible posture toward the gaming industry, but Trump has repeatedly explained that he has made political contributions over the years in an attempt to curry favor with elected officials. A Bush aide told CNN that Trump did not personally lobby Bush to change the state's gambling laws.
Trump spokeswoman Hope Hicks did not respond to multiple requests for comment. But the candidate made his position clear in a July interview with the Wall Street Journal:
"As a businessman and a very substantial donor to very important people, when you give, they do whatever the hell you want them to do," he told the paper.
Trump has repeatedly acknowledged his role as part of a "broken system," explaining that he donated to both Republicans and Democrats to grease the wheels for his business interests. And in the process, Trump has vowed to upend that system by self-funding his campaign and keeping his campaign war chest devoid of any money from lobbyists and special interests.
"Donald Trump has repeatedly admitted he tried to buy politicians. That's not how Jeb works," Bush campaign spokesman Matt Gorman told CNN.